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C-N Coupling Chemistry as a Means to Achieve a Complicated Molecular Architecture: the AR-A2 Case Story
AstraZeneca, UK.ORCID iD: 0000-0001-5781-1689
RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development.
AstraZeneca, Sweden.
AstraZeneca, Sweden.
2013 (English)In: Transition Metal-Catalyzed Couplings in Process Chemistry: Case Studies From the Pharmaceutical Industry, Wiley-VCH Verlag , 2013, p. 73-89Chapter in book (Other academic)
Abstract [en]

A major drug project in the neuroscience area aimed at designing and developing a viable manufacturing process for AR-A2. This turned out to be a tough challenge that resulted in the use of three different synthetic routes. One step to be included from the very start was a Pd-catalyzed C-N bond formation, and this was retained throughout the later versions of the synthesis. At the time of initiating this project in 1998, the combined Buchwald and Hartwig protocols for effecting the chemistry in question-coupling of a N-containing moiety to an aromatic nucleus had only been known for a few years. Therefore, a lot of experimentation was needed to increase the insight and understanding of the chemistry to optimize the performance to fit for large-scale application. The outcome of the efforts resulted in successfully carrying out the chemical transformation is described in detail in this chapter.

Place, publisher, year, edition, pages
Wiley-VCH Verlag , 2013. p. 73-89
Keywords [en]
AR-A2 antagonist, Buchwald-Hartwig coupling, C-N coupling, Chemical transformation, Palladium compounds, Reaction kinetics, Buchwald-hartwig couplings, C-n bond formations, Chemical transformations, Large-scale applications, Manufacturing process, Molecular architecture, Synthetic routes, Chemical bonds
National Category
Engineering and Technology
Identifiers
URN: urn:nbn:se:ri:diva-49932DOI: 10.1002/9783527658909.ch06Scopus ID: 2-s2.0-84886424882ISBN: 9783527658909 (print)ISBN: 9783527332793 (print)OAI: oai:DiVA.org:ri-49932DiVA, id: diva2:1484613
Available from: 2020-10-29 Created: 2020-10-29 Last updated: 2023-10-31Bibliographically approved

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Federsel, Hans-Jürgen

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CiteExportLink to record
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